rac-3-[(Anilino)(naphthalen-2-yl)­methyl]thian-4-one

Harms, K.; Abaee, M.S.; Mojtahedi, M.M.; Mesbah, A.W.

doi:10.1107/S1600536812005983

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o749

doi:10.1107/S1600536812005983

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rac-3-[(Anilino)(naphthalen-2-yl)methyl]thian-4-one

Klaus Harms,^a ^* M. Saeed Abaee,^b Mohammad M. Mojtahedi ^b and A. Wahid Mesbah ^b

^aFachbereich Chemie, Philipps Universität Marburg, Hans Meerwein Strasse, Marburg, D-35032, Germany, and ^bDepartment of Organic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran
^*Correspondence e-mail: harms@chemie.uni-marburg.de

(Received 17 January 2012; accepted 10 February 2012; online 17 February 2012)

In the title compound, C₂₂H₂₁NOS, the thiopyranone ring adopts a chair-like conformation with the substituent in the axial position. The relative configuration of the racemic compound is 3R,7S according to the numbering scheme used in this publication. In the crystal packing, centrosymmetric dimers are built up via N—H⋯O hydrogen bonds, with graph set R₂²(8).

Related literature

For the preparation and spectroscopic characterization of the title compound and a series of related compounds, see: Abaee et al. (2012 ). For the crystal structure of rac-3-[(3-chloroanilino)(4-chlorophenyl)methyl]thian-4-one, see: Harms et al. (2012 ). For the crystal structures of related compounds, see: Guo et al. (2007 ); Fun et al. (2009 ). For patterns in hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₂H₂₁NOS
M_r = 347.46
Monoclinic, P 2₁ /n
a = 10.8049 (10) Å
b = 10.5497 (15) Å
c = 16.4936 (16) Å
β = 97.141 (8)°
V = 1865.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 193 K
0.45 × 0.45 × 0.36 mm

Data collection

Stoe IPDS I diffractometer
Absorption correction: integration [X-AREA and X-RED32 (Stoe & Cie, 2006 )] T_min = 0.942, T_max = 0.960
13547 measured reflections
3244 independent reflections
1939 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.074
S = 0.79
3244 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O1ⁱ	0.926 (15)	2.121 (16)	3.0450 (18)	175.4 (13)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: EXPOSE (Stoe & Cie, 1994 ); cell refinement: CELL (Stoe & Cie, 1994); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: publCIF (Westrip, 2010 ), PLATON (Spek, 2009 ), and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005983/fj2509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005983/fj2509Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005983/fj2509Isup3.cml

checkCIF report

Related literature top

For the preparation and spectroscopic characterization of the title compound and a series of related compounds, see: Abaee et al. (2012). For the crystal structure of (4-chlorophenyl)(3-chlorophenylamino)methyl)dihydro-2H-thiopyran-4(3H)-one [Please check and match brackets], see: Harms et al. (2012). For the crystal structures of related compounds, see: Guo et al. (2007); Fun et al. (2009). For patterns in hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

The title compound is an example of a series of products of an anti-selective three-component Mannich reaction in the thiopyran-4-one system; see Abaee et al. (2012) for details. Colourless crystals suitable for crystal structure determination were grown from ethyl acetate.

Computing details top

Data collection: EXPOSE (Stoe & Cie, 1994); cell refinement: CELL (Stoe & Cie, 1994); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010), PLATON (Spek, 2009), and WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as small spheres of arbitrary radius. Dotted lines indicate hydrogen bonds to the neighbouring molecule generated by crystallographic inversion symmetry. For symmetry code (i), see Table 1.

rac-3-[(Anilino)(naphthalen-2-yl)methyl]thian-4-one top

Crystal data top

C₂₂H₂₁NOS	F(000) = 736
M_r = 347.46	D_x = 1.237 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7999 reflections
a = 10.8049 (10) Å	θ = 2.3–26.0°
b = 10.5497 (15) Å	µ = 0.18 mm⁻¹
c = 16.4936 (16) Å	T = 193 K
β = 97.141 (8)°	Nugget, colourless
V = 1865.5 (4) Å³	0.45 × 0.45 × 0.36 mm
Z = 4

Data collection top

Stoe IPDS I diffractometer	3244 independent reflections
Radiation source: fine-focus sealed tube	1939 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.4°, θ_min = 2.1°
rotation method scans	h = −13→12
Absorption correction: integration [X-AREA and X-RED32 (Stoe & Cie, 2006)]	k = −12→12
T_min = 0.942, T_max = 0.960	l = −19→19
13547 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.79	w = 1/[σ²(F_o²) + (0.0399P)²] where P = (F_o² + 2F_c²)/3
3244 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₂H₂₁NOS	V = 1865.5 (4) Å³
M_r = 347.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8049 (10) Å	µ = 0.18 mm⁻¹
b = 10.5497 (15) Å	T = 193 K
c = 16.4936 (16) Å	0.45 × 0.45 × 0.36 mm
β = 97.141 (8)°

Data collection top

Stoe IPDS I diffractometer	3244 independent reflections
Absorption correction: integration [X-AREA and X-RED32 (Stoe & Cie, 2006)]	1939 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.960	R_int = 0.044
13547 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.79	Δρ_max = 0.23 e Å⁻³
3244 reflections	Δρ_min = −0.37 e Å⁻³
230 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.06564 (5)	0.68462 (6)	0.53056 (4)	0.0733 (2)
O1	0.38884 (11)	0.55992 (11)	0.42256 (7)	0.0481 (3)
N8	0.48932 (11)	0.69693 (12)	0.59618 (8)	0.0318 (3)
H8	0.5282 (14)	0.6206 (15)	0.5880 (10)	0.033 (4)*
C2	0.16654 (16)	0.55096 (17)	0.55576 (14)	0.0568 (6)
H2A	0.1584	0.5237	0.6123	0.068*
H2B	0.1386	0.4798	0.5188	0.068*
C3	0.30417 (14)	0.57832 (15)	0.54910 (11)	0.0359 (4)
H3	0.3517	0.4977	0.5611	0.043*
C4	0.32089 (15)	0.61845 (15)	0.46296 (11)	0.0381 (4)
C5	0.24585 (19)	0.72936 (18)	0.42754 (13)	0.0579 (6)
H5A	0.2618	0.7424	0.3703	0.070*
H5B	0.2728	0.8067	0.4588	0.070*
C6	0.1050 (2)	0.7089 (2)	0.42969 (16)	0.0808 (8)
H6A	0.0776	0.6344	0.3956	0.097*
H6B	0.0591	0.7838	0.4055	0.097*
C7	0.36003 (13)	0.67883 (14)	0.61120 (10)	0.0301 (4)
H7	0.3141	0.7603	0.5991	0.036*
C9	0.56671 (14)	0.78247 (14)	0.64329 (10)	0.0306 (4)
C10	0.52229 (16)	0.89433 (15)	0.67309 (11)	0.0414 (4)
H10	0.4354	0.9118	0.6656	0.050*
C11	0.60450 (18)	0.98055 (17)	0.71379 (12)	0.0519 (5)
H11	0.5731	1.0574	0.7333	0.062*
C12	0.73045 (18)	0.95712 (18)	0.72650 (13)	0.0542 (5)
H12	0.7860	1.0172	0.7541	0.065*
C13	0.77470 (17)	0.84535 (18)	0.69860 (12)	0.0494 (5)
H13	0.8615	0.8275	0.7078	0.059*
C14	0.69458 (15)	0.75867 (16)	0.65734 (11)	0.0396 (4)
H14	0.7268	0.6819	0.6383	0.047*
C15	0.34684 (14)	0.64065 (13)	0.69838 (10)	0.0309 (4)
C16	0.25886 (15)	0.69614 (14)	0.74005 (11)	0.0362 (4)
H16	0.2072	0.7609	0.7141	0.043*
C17	0.24295 (15)	0.65944 (15)	0.82070 (11)	0.0358 (4)
C18	0.14989 (17)	0.71312 (17)	0.86377 (12)	0.0484 (5)
H18	0.0965	0.7772	0.8386	0.058*
C19	0.1364 (2)	0.67372 (18)	0.94068 (12)	0.0561 (6)
H19	0.0730	0.7099	0.9685	0.067*
C20	0.21464 (19)	0.58064 (17)	0.97926 (12)	0.0551 (6)
H20	0.2039	0.5538	1.0329	0.066*
C21	0.30610 (18)	0.52812 (16)	0.94044 (11)	0.0457 (5)
H21	0.3597	0.4660	0.9677	0.055*
C22	0.32231 (15)	0.56508 (14)	0.85973 (11)	0.0353 (4)
C23	0.41391 (15)	0.51076 (15)	0.81611 (11)	0.0385 (4)
H23	0.4686	0.4481	0.8417	0.046*
C24	0.42500 (14)	0.54655 (14)	0.73845 (11)	0.0354 (4)
H24	0.4866	0.5076	0.7104	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0349 (2)	0.0790 (4)	0.1041 (6)	−0.0052 (3)	0.0016 (3)	−0.0435 (4)
O1	0.0546 (7)	0.0537 (7)	0.0350 (8)	0.0127 (6)	0.0011 (7)	−0.0116 (6)
N8	0.0310 (7)	0.0330 (7)	0.0325 (9)	−0.0052 (6)	0.0084 (6)	−0.0056 (6)
C2	0.0460 (11)	0.0515 (11)	0.0727 (16)	−0.0199 (9)	0.0067 (11)	−0.0201 (10)
C3	0.0378 (9)	0.0311 (8)	0.0383 (12)	−0.0046 (7)	0.0032 (8)	−0.0072 (7)
C4	0.0410 (9)	0.0359 (9)	0.0348 (12)	−0.0004 (8)	−0.0054 (9)	−0.0129 (8)
C5	0.0824 (14)	0.0510 (11)	0.0378 (13)	0.0241 (10)	−0.0030 (11)	−0.0043 (9)
C6	0.0664 (14)	0.0796 (16)	0.085 (2)	0.0312 (12)	−0.0363 (13)	−0.0339 (14)
C7	0.0305 (8)	0.0311 (8)	0.0293 (10)	−0.0030 (7)	0.0062 (7)	−0.0028 (7)
C9	0.0353 (8)	0.0343 (8)	0.0222 (10)	−0.0076 (7)	0.0031 (8)	0.0042 (7)
C10	0.0392 (9)	0.0390 (9)	0.0449 (13)	−0.0053 (8)	0.0005 (9)	−0.0058 (8)
C11	0.0577 (12)	0.0432 (10)	0.0518 (15)	−0.0085 (9)	−0.0048 (11)	−0.0117 (9)
C12	0.0549 (12)	0.0532 (12)	0.0490 (15)	−0.0191 (10)	−0.0154 (10)	−0.0005 (10)
C13	0.0380 (9)	0.0556 (12)	0.0508 (14)	−0.0110 (9)	−0.0100 (9)	0.0116 (10)
C14	0.0399 (9)	0.0402 (9)	0.0379 (12)	−0.0031 (8)	0.0022 (9)	0.0073 (8)
C15	0.0303 (8)	0.0294 (8)	0.0337 (11)	−0.0061 (7)	0.0067 (8)	−0.0040 (7)
C16	0.0391 (8)	0.0338 (9)	0.0364 (12)	0.0022 (7)	0.0077 (8)	−0.0008 (8)
C17	0.0424 (9)	0.0331 (9)	0.0336 (11)	−0.0021 (7)	0.0118 (9)	−0.0048 (7)
C18	0.0591 (11)	0.0453 (10)	0.0440 (13)	0.0128 (9)	0.0188 (10)	−0.0016 (9)
C19	0.0763 (14)	0.0537 (11)	0.0440 (14)	0.0113 (11)	0.0299 (12)	−0.0060 (10)
C20	0.0856 (15)	0.0481 (11)	0.0354 (12)	0.0026 (11)	0.0228 (12)	−0.0021 (9)
C21	0.0627 (12)	0.0381 (9)	0.0371 (12)	0.0003 (9)	0.0097 (10)	−0.0001 (8)
C22	0.0419 (9)	0.0314 (8)	0.0336 (11)	−0.0044 (7)	0.0082 (8)	−0.0027 (7)
C23	0.0382 (9)	0.0347 (9)	0.0432 (13)	0.0030 (7)	0.0078 (9)	0.0023 (8)
C24	0.0325 (8)	0.0356 (9)	0.0398 (12)	0.0012 (7)	0.0114 (8)	0.0000 (8)

Geometric parameters (Å, º) top

S1—C6	1.786 (3)	C11—H11	0.9500
S1—C2	1.799 (2)	C12—C13	1.373 (3)
O1—C4	1.2190 (18)	C12—H12	0.9500
N8—C9	1.398 (2)	C13—C14	1.379 (2)
N8—C7	1.4614 (18)	C13—H13	0.9500
N8—H8	0.926 (15)	C14—H14	0.9500
C2—C3	1.532 (2)	C15—C16	1.372 (2)
C2—H2A	0.9900	C15—C24	1.413 (2)
C2—H2B	0.9900	C16—C17	1.416 (2)
C3—C4	1.515 (2)	C16—H16	0.9500
C3—C7	1.544 (2)	C17—C22	1.415 (2)
C3—H3	1.0000	C17—C18	1.419 (2)
C4—C5	1.500 (2)	C18—C19	1.360 (3)
C5—C6	1.542 (3)	C18—H18	0.9500
C5—H5A	0.9900	C19—C20	1.397 (3)
C5—H5B	0.9900	C19—H19	0.9500
C6—H6A	0.9900	C20—C21	1.361 (2)
C6—H6B	0.9900	C20—H20	0.9500
C7—C15	1.517 (2)	C21—C22	1.419 (2)
C7—H7	1.0000	C21—H21	0.9500
C9—C10	1.387 (2)	C22—C23	1.415 (2)
C9—C14	1.395 (2)	C23—C24	1.355 (2)
C10—C11	1.385 (2)	C23—H23	0.9500
C10—H10	0.9500	C24—H24	0.9500
C11—C12	1.373 (3)

C6—S1—C2	96.89 (10)	C12—C11—C10	121.29 (18)
C9—N8—C7	120.55 (12)	C12—C11—H11	119.4
C9—N8—H8	113.1 (10)	C10—C11—H11	119.4
C7—N8—H8	111.8 (9)	C13—C12—C11	118.89 (17)
C3—C2—S1	113.67 (13)	C13—C12—H12	120.6
C3—C2—H2A	108.8	C11—C12—H12	120.6
S1—C2—H2A	108.8	C12—C13—C14	120.76 (17)
C3—C2—H2B	108.8	C12—C13—H13	119.6
S1—C2—H2B	108.8	C14—C13—H13	119.6
H2A—C2—H2B	107.7	C13—C14—C9	120.70 (16)
C4—C3—C2	110.49 (16)	C13—C14—H14	119.7
C4—C3—C7	110.36 (12)	C9—C14—H14	119.7
C2—C3—C7	112.62 (13)	C16—C15—C24	118.46 (15)
C4—C3—H3	107.7	C16—C15—C7	120.95 (14)
C2—C3—H3	107.7	C24—C15—C7	120.59 (13)
C7—C3—H3	107.7	C15—C16—C17	121.78 (15)
O1—C4—C5	121.02 (17)	C15—C16—H16	119.1
O1—C4—C3	121.42 (15)	C17—C16—H16	119.1
C5—C4—C3	117.49 (15)	C22—C17—C16	118.82 (14)
C4—C5—C6	111.66 (17)	C22—C17—C18	118.67 (16)
C4—C5—H5A	109.3	C16—C17—C18	122.51 (16)
C6—C5—H5A	109.3	C19—C18—C17	120.67 (17)
C4—C5—H5B	109.3	C19—C18—H18	119.7
C6—C5—H5B	109.3	C17—C18—H18	119.7
H5A—C5—H5B	107.9	C18—C19—C20	120.71 (17)
C5—C6—S1	113.05 (16)	C18—C19—H19	119.6
C5—C6—H6A	109.0	C20—C19—H19	119.6
S1—C6—H6A	109.0	C21—C20—C19	120.40 (18)
C5—C6—H6B	109.0	C21—C20—H20	119.8
S1—C6—H6B	109.0	C19—C20—H20	119.8
H6A—C6—H6B	107.8	C20—C21—C22	120.76 (18)
N8—C7—C15	113.57 (13)	C20—C21—H21	119.6
N8—C7—C3	106.28 (12)	C22—C21—H21	119.6
C15—C7—C3	111.80 (12)	C23—C22—C17	118.42 (15)
N8—C7—H7	108.3	C23—C22—C21	122.78 (16)
C15—C7—H7	108.3	C17—C22—C21	118.79 (15)
C3—C7—H7	108.3	C24—C23—C22	121.16 (15)
C10—C9—C14	118.27 (15)	C24—C23—H23	119.4
C10—C9—N8	122.46 (14)	C22—C23—H23	119.4
C14—C9—N8	119.17 (14)	C23—C24—C15	121.34 (14)
C11—C10—C9	120.08 (16)	C23—C24—H24	119.3
C11—C10—H10	120.0	C15—C24—H24	119.3
C9—C10—H10	120.0

C6—S1—C2—C3	57.57 (16)	N8—C9—C14—C13	175.40 (15)
S1—C2—C3—C4	−59.40 (17)	N8—C7—C15—C16	135.46 (15)
S1—C2—C3—C7	64.52 (19)	C3—C7—C15—C16	−104.28 (16)
C2—C3—C4—O1	−121.46 (17)	N8—C7—C15—C24	−44.72 (19)
C7—C3—C4—O1	113.33 (16)	C3—C7—C15—C24	75.54 (18)
C2—C3—C4—C5	55.62 (19)	C24—C15—C16—C17	−1.5 (2)
C7—C3—C4—C5	−69.58 (19)	C7—C15—C16—C17	178.33 (14)
O1—C4—C5—C6	121.38 (19)	C15—C16—C17—C22	1.6 (2)
C3—C4—C5—C6	−55.7 (2)	C15—C16—C17—C18	−178.03 (16)
C4—C5—C6—S1	59.1 (2)	C22—C17—C18—C19	−0.7 (3)
C2—S1—C6—C5	−56.56 (16)	C16—C17—C18—C19	178.91 (18)
C9—N8—C7—C15	−56.27 (19)	C17—C18—C19—C20	0.7 (3)
C9—N8—C7—C3	−179.60 (14)	C18—C19—C20—C21	0.2 (3)
C4—C3—C7—N8	−54.62 (17)	C19—C20—C21—C22	−1.1 (3)
C2—C3—C7—N8	−178.61 (15)	C16—C17—C22—C23	−0.4 (2)
C4—C3—C7—C15	−179.05 (13)	C18—C17—C22—C23	179.22 (15)
C2—C3—C7—C15	56.96 (19)	C16—C17—C22—C21	−179.83 (15)
C7—N8—C9—C10	−34.1 (2)	C18—C17—C22—C21	−0.2 (2)
C7—N8—C9—C14	149.59 (15)	C20—C21—C22—C23	−178.28 (17)
C14—C9—C10—C11	1.6 (2)	C20—C21—C22—C17	1.1 (3)
N8—C9—C10—C11	−174.77 (16)	C17—C22—C23—C24	−0.8 (2)
C9—C10—C11—C12	−0.8 (3)	C21—C22—C23—C24	178.61 (17)
C10—C11—C12—C13	−0.5 (3)	C22—C23—C24—C15	0.9 (2)
C11—C12—C13—C14	1.0 (3)	C16—C15—C24—C23	0.3 (2)
C12—C13—C14—C9	−0.2 (3)	C7—C15—C24—C23	−179.57 (15)
C10—C9—C14—C13	−1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1ⁱ	0.926 (15)	2.121 (16)	3.0450 (18)	175.4 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁NOS
M_r	347.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	10.8049 (10), 10.5497 (15), 16.4936 (16)
β (°)	97.141 (8)
V (Å³)	1865.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.45 × 0.45 × 0.36

Data collection
Diffractometer	Stoe IPDS I diffractometer
Absorption correction	Integration [X-AREA and X-RED32 (Stoe & Cie, 2006)]
T_min, T_max	0.942, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13547, 3244, 1939
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.074, 0.79
No. of reflections	3244
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.37

Computer programs: EXPOSE (Stoe & Cie, 1994), CELL (Stoe & Cie, 1994), X-RED32 (Stoe & Cie, 2006), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), publCIF (Westrip, 2010), PLATON (Spek, 2009), and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1ⁱ	0.926 (15)	2.121 (16)	3.0450 (18)	175.4 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

References

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Volume 68| Part 3| March 2012| Page o749

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